


How I Wanted You

by justanotherbusyfangirl



Category: Supernatural
Genre: F/M, Loss of Virginity, Vaginal Sex
Language: English
Status: Completed
Published: 2018-01-14
Updated: 2018-01-14
Packaged: 2019-09-03 00:12:40
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 3,008
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/16797550
Author URL: https://archiveofourown.org/users/justanotherbusyfangirl/pseuds/justanotherbusyfangirl
Summary: It's just how you wanted Dean, even if he wasn't expecting it.





	How I Wanted You

* * *

You felt the flush of your cheeks, the heat pooling between your legs with every glance Dean shot your way. Those looks had never been sent your way before, rather to the girls he would meet in the bars and disappear with for the night.

Tonight was different, though. To your humiliation, Sam – sweet Sam, best friend Sam, Sammy who you might have to _murder_ later on – had blabbed to Dean about your feelings for him. Dean took it as a joke when Sam said it at first, but you thought maybe, just maybe, he was taking it a little more seriously now.

A couple beers in and one pool hustle down, Dean had started sending you some glances across the table.

Another beer later and Sam was ready to go. “You coming or staying, Y/N?” he asked, his kind nature always shining through. You glanced at Dean, unsure of what you wanted.

The heated gaze and tilt of his head answered for you. 

“I’ll stay a while longer, thanks Sam.”

Sam nodded and left, leaving you and Dean at the bar, alone amongst the locals. “Pool?” Dean asked simply, making you smile.

The two of you played a while longer, the ‘accidental’ brushes and bumps against one another getting more and more frequent. You beat Dean (because you always beat Dean), whooping in celebration and throwing your arms in the air.

Dean’s wrapped around your waist, picking you up and twirling you around in a circle to celebrate with you. He’d done that a thousand times before, but this time when he set your feet back on the ground he didn’t let go of your waist.

Your hands were settled on his shoulders for balance and you didn’t move them either.

The two of you studied each other’s faces for a moment before Dean leaned in slightly. “Was Sammy telling the truth, earlier?”

You gulped.

“Yeah,” you breathed. No use in denying it, you figured now that Dean knew, he had probably begun to notice all of the little things you said or did around him that indicated your feelings. You couldn’t look away from his face, trying to read the response in his eyes.

“Hmm,” he hummed thoughtfully, raising a hand to tuck a strand of hair behind your ear. His thumb caressed your cheek for a second before he leaned even closer. His eyes drifted toward your lips and back to yours in a question. It was a question he didn’t need to ask, but you nodded your head minutely, eyes begging him to kiss you.

So he did.

His lips brushed against yours with tenderness, his hand still cupping your face. Your fingers grasped at his shoulders as he sucked your bottom lip between his own before kissing it again. He pulled your body closer to his so that you were pressed together from knee to chest, the heat of his skin warming you through layers of clothing.

He ended the kiss before you wanted him to, but the words he said when his lips left yours were worth it.

“Let’s get out of here.”

You followed Dean without even thinking, willing to follow him anywhere. Hell, you’d followed him into many a dangerous situation with various monsters, following him _out of here_ , especially with the implication those words had, didn’t need a second thought.

The motel you were staying in was right next door to the bar, and they’d actually had two rooms at a fairly decent price when the three of you checked in. You took out the key to your single room, holding it out for Dean.

He looked at it then back at your face, understanding on his face that you wanted this, too. He grabbed the key in one hand and your hand in his other, practically dragging you across the parking lot and to your door. He opened it for you, letting you inside first before closing and locking the door behind you.  
You stood in the middle of the room, somewhat awkwardly, while Dean leaned back against the closed door.

“Never thought I’d see the day,” he mumbled, and you weren’t sure if the words were for you or him. Before you could think too hard about them, he launched himself off the door and toward you, his arms wrapping around you again. “Y/N…”

His mouth was on yours again, but this kiss was more intense than the one at the bar had been. Dean’s tongue was sliding along your lips immediately, diving in when you allowed him access. He tasted like the beer and peanuts you’d been having at the bar, with a hint of something distinctly Dean underneath it all. Your hands wrapped around his neck to hold on, because this kiss was more than any other you’d ever had before.

Your body was hot, the feeling of Dean pressed against you doing all sorts of things to your skin. Tingles ran up and down your spine as Dean’s fingertips dug into your hips before they slipped under the hem of your shirt, tickling the skin they found there.

You moaned into Dean’s mouth which seemed to set him into motion. Without breaking the kiss, he guided you back until your legs hit the bed, lowering you slowly down. The two of you scootched to the center of the bed so that your head was resting on the pillows, Dean’s body covering yours halfway. His mouth was back on yours as he tucked a leg between yours, grabbing at your outer leg to wrap it around his body. His huge hand slid up your thigh until it rested on your ass, squeezing gently.

Your hands tangled into Dean’s hair, just trying to hold on to something as he took control. You’d never felt like this before, your whole body was on fire. There was a heat pooling between your legs and your hips arched upward to press into Dean, letting you feel the growing line of his erection against your waist.

Dean began kissing along your jaw and down your neck, drawing whimpers from your mouth. “Dean…” you whispered, not knowing if it was a question or request, just feeling the need to say his name.

“Oh, sweetheart, I shoulda done this a long time ago,” he mumbled against your collarbone before he sat back, pulling his shirts off as quickly as he could. Your eyes were locked on the skin as it was revealed to you until he helped you sit up as well, pulling off your top. You crossed your arms, trying to cover yourself slightly, but Dean’s hands grabbed your wrists and held them still.

“Don’t hide from me, Y/N. You’re gorgeous,” he told you, the insistence in his voice making you nod. 

You couldn’t admit to Dean that this was the least dressed you’d ever been in front of someone who wasn’t immediate family. 

That thought flew away when he returned to where he’d been kissing along your collarbone, this time unhindered from moving southward by clothing. He nuzzled along the swell of your bra until his scruffy face was settled in the middle of your chest. “So gorgeous…” he repeated, before slipping a hand underneath you and unclasping your bra.

You arched your back automatically, allowing Dean to slip the fabric from your shoulders and throw it across the room. He didn’t give you time to breathe or be nervous before his mouth was laving praises onto your nipples, his fingers occupying the other one while he worked.

You groaned, hands finding purchase in his hair again as he moved to settle himself between your legs. His warm chest pressed against your stomach and made you want more, one hand trailing down to scratch and pull at the muscles of his back.

When Dean was satisfied with the attention he’d given to your breasts, his mouth moved further down your body, sucking at sensitive places he found on your stomach before he was stopped at the waist of your jeans. You held your breath as his fingers slid teasingly under the fabric, hands meeting in the middle to unbutton and unzip slowly.

Your hands grabbed at the sheets on either side of your waist while you let Dean strip your jeans down your legs, taking your shoes and socks off with them. He stood at the foot of the bed and rid himself of his own jeans, losing his boxers at the same time.

Your eyes couldn’t help themselves, drawn to the hard erection standing proud before you. He was Adonis; his chest was strong but not chiseled, his hips the perfect proportion to his shoulders. His bowlegs were sexy as hell, his hard cock the center of it all.

Dean’s eyes were heated as he watched you, watching him. He stood there for a minute as you took in each other, you still with your underwear on and him completely bare. Finally he snapped out of it, grabbing his wallet – getting a condom, you realized – from his jeans before crawling back up the bed to cover you with his body.

He settled back between your legs, his erection pressing against the cotton of your panties. He kissed you firmly, his hands grasping at the sides of your face. There was more in that kiss than you’d expected, more need and yearning.

You felt the same, hoped that you were expressing the same need for him as he was for you.

One of his hands trailed back down your body as he kissed you, the kiss distracting you enough that you were slightly surprised when his fingers rubbed at your pussy through your panties. You were wet, embarrassingly so, but the realization of that made Dean moan into your mouth.

Swiftly, he pushed the underwear to one side, slipping a finger inside of you. Your body lurched in response, feeling things you’d never felt before.

Dean seemed satisfied with just a little bit of teasing between your legs, because he pushed off of you enough to slide your underwear down your legs and settle the condom onto himself.

You watched with wide eyes, glad that he was occupied for the moment. This was it, and you wouldn’t have it any other way.

When Dean was happy with the condom, his attention returned to you. “Ready?” he asked, sweetly.

“Yeah,” you breathed, letting him grasp one of your hands in his, threading your fingers together and pressing it into the pillow next to your head. His other hand lined himself up with your entrance as he tucked his head into the crook of your neck.

He kissed you hard there, with a little bit of teeth involved as well, as he pressed inside of you. One fluid movement had him firmly seated in your cunt, the barrier inside of you stretched and broken for the first time.

As much as you tried to hold them back – because this was _Dean_ and Dean was _everything_ and if you’d had to choose anyone in the whole world, it would always be _Dean_ – tears leaked from the edges of your eyes at the pain and stretch. A small cry left your throat of it’s own accord. Your body tensed, your knees bending, legs folding upward, and holding Dean still inside of you.

Your eyes clenched shut, trying their best to not let any more tears out. You didn’t want Dean to see you hurting. Sex was supposed to feel good, you knew that it would after the initial stretch, but you just hoped that feeling would come fast. You bit your bottom lip, holding in the whimpers that threatened to escape.

All of that happened in a split second, while Dean’s face was tucked into your neck, but your small, held-back reaction was enough for him to know.

He pulled his face back from where it hid so that he could look at you. Even though your eyes were closed, you could imagine the look on his face. 

“Y/N?” he asked as his free hand, the one not holding tightly onto yours, brushed the tears away from where they’d fallen. “Y/N, what –“

You opened your eyes, meeting his. Yes, that was confusion and surprise on his face, and then realization. You flushed, emotions running wild inside of you, so much that you weren’t sure if you would be able to keep them down.

“Why didn’t you tell me, you should have said something…Y/N,” Dean babbled, keeping his lower body completely still. You shook your head, unsure of whether your voice would be strong enough to speak. “Y/N, why didn’t you tell me you were a virgin?”

You looked away then, eyes moving to the ugly wallpaper next to the bed. “Y/N, you should have said something. I would have done things so differently, I would have…”

“I didn’t want things to happen differently,” you interrupted stubbornly. “This is how I wanted it, this is how I wanted _you_.”

Your words gave you confidence to look back at Dean. He sighed, knowing you well enough that he understood what you were saying. You were afraid that if he knew you were a virgin, he wouldn’t have had sex with you at all.

“Y/N, if I’d known, I would have taken things slower,” Dean insisted. “I would have worked you with my fingers until you were dripping, I would have eased my way inside of you. I wouldn’t have assumed that you were ready, that you could take me. Fuck, I just hurt you, I can tell. I never want to hurt you, ever.”

His sincere words caused more tears to escape, this time not from pain but from the tenderness that Dean was showing you. Your free hand came up to cup his cheek as you smiled.

“It’s okay, Dean. We can do all of that another time. I wanted this, and I don’t want to change a thing. Please.”

Your head reached up to kiss Dean softly on the lips, trying to convince him you’d be okay. He responded with a passion, trying to care for you in the kiss the way he hadn’t cared a few minutes before.

“I’m going to make this better,” he murmured against your lips. “Just tell me if I need to do anything different. I want you to fly, Y/N, I’m going to get you there.”  
You nodded, your arms both wrapping around Dean’s neck as he got a better position above you, one hand propping himself up and the other resting on your hip. The pull of his cock out of your tightness had you grimacing, but it wasn’t as painful as when he’d entered you initially. 

He began thrusting shallowly and slowly, not bottoming out like he’d done on the first thrust. After a minute of that, the pain was leaving and it was feeling better…strange, but better. 

Dean noticed the change in your disposition, because he began going a little deeper with each thrust then, angling his hips a little differently so that he was brushing your clit with each pass.

Your legs fell open, relaxed and needy. “Dean…” you groaned after a particularly sensual twist of his hips. You were gone, pliant under his touch, and he knew you were ready for more.

“That’s it, Y/N,” he said, sucking your earlobe between his lips. “Relax, let me take care of you.”

His hips moved with purpose, making sure that your clit was stimulated at the same time he hit places inside you that you didn’t know existed. Your body was tingling with pleasure with every move he made, building up to something that you couldn’t predict.

It was all getting to be too much, the sensations overwhelming you and your hands grasping at Dean’s back for purchase. You were embarrassed by the noises you were making but they only seemed to urge Dean on, as if he were able to interpret every groan and hiss you made into a language he understood.

When the coil in your lower belly was wound tighter than you could imagine, Dean slipped a hand between your bodies to brush against your clit. A few more deep pumps of his cock into your heat and his mouth dominating yours once more in a kiss threw you off the cliff, Dean’s name a cry of pleasure on your lips as you came unraveled underneath him.

Dean worked you through your orgasm, making sure to draw it out just as long as you could handle it. When you were too sensitive anymore, Dean pulled out of you, sitting back on his feet and removing the condom. He observed you with hooded eyes as he pumped his hand once, twice, three times over his cock before exploding, his come hitting your leg and the bedspread below.

The two of you were still except for your labored breathing, just staring at each other in the aftermath. Dean came out of the stupor first, going to the bathroom to dampen a washcloth and come back, wiping the mess of pleasure from between your legs, your thigh, and the bed. He tossed the condom in the trash and threw the cloth back toward the bathroom before returning to you, maneuvering your heavy body beneath the covers.

“You should have told me, Y/N,” Dean brought up again as he tucked you under his arm. “I wish…”

“Hush, Dean,” you interrupted him. “You did everything right and more. Don’t wish for anything different, because I don’t.”

A heavy sigh from Dean told you that he still didn’t quite agree with you, but he wasn’t going to argue any more tonight. He kissed your forehead, tilted your head upward to catch the tip of your nose, then tilted you more to kiss your lips. You smiled into the kiss but were too tired to respond, something he seemed to understand.

“Rest up, Y/N,” he said, pulling you further against his body. “Sweet dreams.”


End file.
